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In 2003, some two decades after her groundbreaking album She’s So Unusual and the infectious anthem “Girls Just Want To Have Fun” earned her a Grammy for Best New Artist and established her as one of the biggest stars to emerge from the MTV era, Cyndi Lauper has tried to revamp her classic daffy image with a collection of standards called At Last. Although the collection was mostly acclaimed by critics, it would take much more than one album for fans to stop being charmed by the memories of her goofy yet endearing personality, ragamuffin outfits and multi-toned hair—all of which made her a star but detracted from her strong voice and songwriting skills. No other musical icon of the 80s culture can claim to have a hit (“Time After Time”) covered by a legendary jazz musician like Miles Davis.

New York born Cynthia Anne Stephanie Lauper launched her career in the mid-70s as a Manhattan club singer and formed Blue Angel with pianist John Turi. Their 1980 album included wild versions of rock classics and numerous originals, which showcased Lauper’s early songwriting talents. Following the group’s breakup, Lauper sang in local clubs and restaurants until her manager and boyfriend David Wolff got her a deal with Portrait.

Her unique look, rangy, neo-Betty Boop voice, coupled with her over-the-top personality made her a natural for the emerging video phenomenon, and heavy MTV support propelled “Girls Just Want To Have Fun” to the top of the pop charts; it peaked at #2, while the evocative, romantic anthem “Time After Time,” which showcased a more mature and thoughtful artistry and considerable songwriting talent, hit #1 and the next two singles (“She Bop,” and “All Through The Night”) went Top Ten. All in all, an extraordinary debut effort, which got everyone's attention. As well as the Grammy nod, she was Rolling Stone’s Best New Artist and Best Female Video Artist, MTV’s Best Female Video Artist, and she won two American Music Awards. Throughout her breakthrough year, Lauper worked 350 days and logged nearly 300 concerts, performing or promoting She’s So Unusual in 150 cities. She also found time to design all the T-shirts sold at her concerts.

After releasing the hit single "The Goonies 'R' Good Enough," theme song from The Goonies, she returned with True Colors in the fall of 1986. While it was successful — the title track went to number one, and remains a pop classic, and the album peaked at number four and went platinum — its softer, adult-contemporary sound lost Lauper some hardcore fans, who felt she had sold out. Her 1988 appearance as a beautician (her feature film debut) in the notorious bomb Vibes also curtailed her momentum.

Despite the Top Ten hit “I Drove All Night” in 1989 (later a hit and perfume commercial for Celine Dion), her third album A Night To Remember sold poorly, peaking at #37. The next year, she broke up with Wolff and married actor David Thornton. (Little Richard led the couple in the recitation of their non-traditional vows, and Patti Labelle sang the wedding theme "Come What May". )

Lauper was then joined by her former writing partners Ron Hyman and Eric Bazilian for 1993’s critically acclaimed Hat Full Of Stars, a successful mix of soul/pop/hip-hop with a smattering of ethnic/folk. A reworked version of her biggest hit, retitled "Hey, Now (Girls Just Want To Have Fun)," reached number 4 on the UK charts in September 1994, the year of the global release of the compilation Twelve Deadly Cyns…And Then Some; it was released in the U.S. the following year.

Lauper’s acting career finally bore fruit with two Emmy-nominated performances on the sitcom Mad About You in the mid-90s (she won for the second, in 1995); she later appeared on the show in 1999. She released Sisters of Avalon in 1997, the year she had her first child, Declyn. While pregnant, she toured the U.S. for three months with Tina Turner, and the new mom also racked up the miles with Cher in 1999 (and later in 2002).

Her first dramatic film role, in the Christopher Walken vehicle The Opportunists in 1999 met with good reviews.